KR102193270B1 - 말단 유레아 및/또는 우레탄 기를 갖는 신규한 카보다이이미드, 상기 카보다이이미드의 제조방법 및 상기 카보다이이미드의 용도 - Google Patents
말단 유레아 및/또는 우레탄 기를 갖는 신규한 카보다이이미드, 상기 카보다이이미드의 제조방법 및 상기 카보다이이미드의 용도 Download PDFInfo
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- KR102193270B1 KR102193270B1 KR1020157035329A KR20157035329A KR102193270B1 KR 102193270 B1 KR102193270 B1 KR 102193270B1 KR 1020157035329 A KR1020157035329 A KR 1020157035329A KR 20157035329 A KR20157035329 A KR 20157035329A KR 102193270 B1 KR102193270 B1 KR 102193270B1
- Authority
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- South Korea
- Prior art keywords
- carbodiimide
- formula
- terephthalate
- iii
- pla
- Prior art date
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- 150000001718 carbodiimides Chemical class 0.000 title claims abstract description 92
- 239000004202 carbamide Substances 0.000 title claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 15
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 50
- 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 36
- 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 36
- 239000004626 polylactic acid Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 239000004814 polyurethane Substances 0.000 claims abstract description 20
- 239000004629 polybutylene adipate terephthalate Substances 0.000 claims abstract description 18
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims abstract description 18
- 229920002961 polybutylene succinate Polymers 0.000 claims abstract description 17
- 239000004631 polybutylene succinate Substances 0.000 claims abstract description 17
- 229920001707 polybutylene terephthalate Polymers 0.000 claims abstract description 17
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims abstract description 14
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims abstract description 14
- 229920006346 thermoplastic polyester elastomer Polymers 0.000 claims abstract description 14
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 14
- 238000009472 formulation Methods 0.000 claims abstract description 10
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
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- 150000003077 polyols Chemical class 0.000 claims abstract description 7
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- 239000003381 stabilizer Substances 0.000 claims abstract description 6
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- 239000000853 adhesive Substances 0.000 claims abstract description 5
- 230000001070 adhesive effect Effects 0.000 claims abstract description 5
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- 238000000576 coating method Methods 0.000 claims abstract description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000005442 diisocyanate group Chemical group 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229920005906 polyester polyol Polymers 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 150000001298 alcohols Chemical class 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000005453 pelletization Methods 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
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- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 238000007306 functionalization reaction Methods 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- BTGGRPUPMPLZNT-PGEUSFDPSA-N 2,2-bis[[(z)-octadec-9-enoyl]oxymethyl]butyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC BTGGRPUPMPLZNT-PGEUSFDPSA-N 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
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- 239000010985 leather Substances 0.000 claims description 2
- 239000002649 leather substitute Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 229940049964 oleate Drugs 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 claims 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
- 229910000071 diazene Inorganic materials 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 229920000903 polyhydroxyalkanoate Polymers 0.000 abstract description 6
- 150000003626 triacylglycerols Chemical class 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZTQDOJXZNGFLOO-UHFFFAOYSA-N N=C=O.N=C=O.CCc1ccc(C)c(CC)c1 Chemical compound N=C=O.N=C=O.CCc1ccc(C)c(CC)c1 ZTQDOJXZNGFLOO-UHFFFAOYSA-N 0.000 description 6
- IIACQPHUGFYLHV-UHFFFAOYSA-N N=C=O.N=C=O.CCc1cccc(CC)c1C Chemical compound N=C=O.N=C=O.CCc1cccc(CC)c1C IIACQPHUGFYLHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- HYJYJUIGMPZFDK-UHFFFAOYSA-N N=C=O.N=C=O.CCC(CC)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.CCC(CC)C1=CC=CC=C1 HYJYJUIGMPZFDK-UHFFFAOYSA-N 0.000 description 2
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 2
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- PZMJNJDRDKPVLB-UHFFFAOYSA-N 2,4-Diaethyl-1-methyl-benzol Natural products CCC1=CC=C(C)C(CC)=C1 PZMJNJDRDKPVLB-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- FEUFNKALUGDEMQ-UHFFFAOYSA-N 2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=O FEUFNKALUGDEMQ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- OJDSGUYSPJFSDM-UHFFFAOYSA-N S=P1=CCCC1 Chemical compound S=P1=CCCC1 OJDSGUYSPJFSDM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003819 basic metal compounds Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
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- KMBWMZQYDLDUQQ-UHFFFAOYSA-N n'-[2,6-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=N KMBWMZQYDLDUQQ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
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- 230000006641 stabilisation Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BWILWWQQPCEBFY-UHFFFAOYSA-N styrene;terephthalic acid Chemical compound C=CC1=CC=CC=C1.OC(=O)C1=CC=C(C(O)=O)C=C1 BWILWWQQPCEBFY-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
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- 150000004072 triols Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C267/00—Carbodiimides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/02—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/027—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing urethodione groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/21—Urea; Derivatives thereof, e.g. biuret
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Biological Depolymerization Polymers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20130167511 EP2803660A1 (de) | 2013-05-13 | 2013-05-13 | Neue Carbodiimide mit endständigen Harnstoff- und/oder Urethangruppen, Verfahren zu deren Herstellung und deren Verwendung |
| EP13167511.8 | 2013-05-13 | ||
| PCT/EP2014/059578 WO2014184116A1 (de) | 2013-05-13 | 2014-05-09 | Neue carbodiimide mit endständigen harnstoff- und/oder urethangruppen, verfahren zu deren herstellung und deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160020434A KR20160020434A (ko) | 2016-02-23 |
| KR102193270B1 true KR102193270B1 (ko) | 2020-12-22 |
Family
ID=48366224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157035329A KR102193270B1 (ko) | 2013-05-13 | 2014-05-09 | 말단 유레아 및/또는 우레탄 기를 갖는 신규한 카보다이이미드, 상기 카보다이이미드의 제조방법 및 상기 카보다이이미드의 용도 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9512299B2 (de) |
| EP (2) | EP2803660A1 (de) |
| JP (1) | JP6162887B2 (de) |
| KR (1) | KR102193270B1 (de) |
| CN (1) | CN105228980B (de) |
| AU (1) | AU2014267409B2 (de) |
| BR (1) | BR112015028599B1 (de) |
| CA (1) | CA2909890C (de) |
| DK (1) | DK2997010T3 (de) |
| ES (1) | ES2657926T3 (de) |
| HU (1) | HUE036514T2 (de) |
| MX (1) | MX367797B (de) |
| NO (1) | NO2997010T3 (de) |
| PL (1) | PL2997010T3 (de) |
| PT (1) | PT2997010T (de) |
| RU (1) | RU2667500C2 (de) |
| SG (1) | SG11201508680VA (de) |
| UA (1) | UA117485C2 (de) |
| WO (1) | WO2014184116A1 (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105778026B (zh) * | 2014-12-25 | 2018-11-20 | 上海华峰新材料研发科技有限公司 | 含位阻的碳化二亚胺类低聚物及其制备方法和应用 |
| EP3307709B1 (de) * | 2015-06-15 | 2019-02-13 | LANXESS Deutschland GmbH | Verfahren zur herstellung von polymeren carbodiimiden unter zusatz von cäsiumsalzen, polymere carbodiimide und deren verwendung |
| CN109153818B (zh) * | 2016-05-09 | 2020-08-07 | 朗盛德国有限责任公司 | 包含碳二亚胺、酯和pvc的组合物，其生产和用途 |
| EP3243871A1 (de) * | 2016-05-09 | 2017-11-15 | LANXESS Deutschland GmbH | Zusammensetzungen enthaltend carbodiimid und ester, deren herstellung und verwendung bei der stabilisierung von polyvinylchlorid |
| EP3260487A1 (de) * | 2016-06-22 | 2017-12-27 | LANXESS Deutschland GmbH | Hydrolysestabile zusammensetzungen für folien in solarzellen |
| EP3431538A1 (de) * | 2017-07-17 | 2019-01-23 | LANXESS Deutschland GmbH | Zusammensetzungen enthaltend polymeres carbodiimid, epoxid und polyester-basierte polymere, deren herstellung und verwendung |
| HUE057882T2 (hu) * | 2017-12-20 | 2022-06-28 | Lanxess Deutschland Gmbh | Eljárás karbodiimidek elõállítására |
| CN108715628B (zh) * | 2018-06-22 | 2022-04-01 | 上海朗亿功能材料有限公司 | 一种脂环族聚碳化二亚胺抗水解剂及其制备方法 |
| EP3670180A1 (de) * | 2018-12-17 | 2020-06-24 | LANXESS Deutschland GmbH | Multischichtsystem aus mindestens 3 polyesterschichten, dessen herstellung und verwendung |
| EP3686239A1 (de) * | 2019-01-23 | 2020-07-29 | LANXESS Deutschland GmbH | Hydrolysestabilisierte polyethylenterephthalat (pet) - haltige zusammensetzungen |
| CN111073264B (zh) * | 2019-12-28 | 2021-08-31 | 温岭东方红车料有限公司 | 一种自行车坐垫及其成型工艺 |
| CN111303595A (zh) * | 2020-04-06 | 2020-06-19 | 浙江本能新材料有限公司 | 一种可降解无机高分子聚合物树脂材料及其制备方法 |
| EP4119541A1 (de) | 2021-07-14 | 2023-01-18 | LANXESS Deutschland GmbH | Neue carbodiimide mit endständigen harnstoff- und/oder urethangruppen, verfahren zu deren herstellung und deren verwendung |
| CN113968954B (zh) * | 2021-12-13 | 2023-07-07 | 福建汇得新材料有限公司 | 一种可降解热塑性聚氨酯弹性体及其制备方法和应用 |
| CN115181038B (zh) * | 2022-08-03 | 2024-06-25 | 万华化学（宁波）有限公司 | 长保质期碳化二亚胺改性异氰酸酯及其制备方法与应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1130594B (de) | 1956-07-30 | 1962-05-30 | Du Pont | Verfahren zur Herstellung von gegebenenfalls modifizierten Polykondensationsprodukten mití¬N?C?N-Brueckengliedern |
| US2941983A (en) | 1957-05-07 | 1960-06-21 | Du Pont | Urethane-terminated polycarbodiimides |
| DE1156401B (de) | 1960-05-24 | 1963-10-31 | Bayer Ag | Verfahren zur Herstellung von Carbodiimiden |
| CA987042A (en) * | 1971-10-05 | 1976-04-06 | General Tire And Rubber Company (The) | Method for making urethane-terminated polycarbodiimides and products thereof |
| DE3512918A1 (de) * | 1985-04-11 | 1986-10-16 | Bayer Ag, 5090 Leverkusen | Carbodiimidgruppen enthaltende isocyanat-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als zusatzmittel fuer waessrige loesungen oder dispersionen von kunststoffen |
| DE4018184A1 (de) * | 1990-06-07 | 1991-12-12 | Bayer Ag | Verfahren zur stabilisierung von estergruppen enthaltenden kunststoffen |
| NL9100578A (nl) * | 1991-04-03 | 1992-11-02 | Stahl Holland Bv | Multifunctionele waterdispergeerbare verknopingsmiddelen. |
| DE4318979A1 (de) | 1993-06-08 | 1994-12-15 | Basf Ag | Carbodiimide und/oder oligomere Polycarbodiimide auf Basis von 1,3-Bis-(1-methyl-1-isocyanato-ethyl)-benzol, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Hydrolysestabilisator |
| US5498747A (en) * | 1994-05-12 | 1996-03-12 | Basf Aktiengesellschaft | Carbodiimides and/or oligomeric polycarbodiimides based on 1,3-bis (1-methyl-1-isocyanatoethyl)benzene, their preparation, and their use as hydrolysis stabilizers |
| DE102004024204A1 (de) * | 2004-05-13 | 2005-12-08 | Basf Ag | Kunststoffe enthaltend Carbodiimid |
| DE102004041605A1 (de) * | 2004-08-26 | 2006-03-02 | Basf Ag | Carbodiimide |
| CN102504161B (zh) * | 2011-10-18 | 2013-07-03 | 池州万维化工有限公司 | 一种碳二亚胺类聚合物及其制备方法与用途 |
-
2013
- 2013-05-13 EP EP20130167511 patent/EP2803660A1/de not_active Withdrawn
-
2014
- 2014-05-09 PL PL14722684T patent/PL2997010T3/pl unknown
- 2014-05-09 JP JP2016513309A patent/JP6162887B2/ja active Active
- 2014-05-09 EP EP14722684.9A patent/EP2997010B1/de active Active
- 2014-05-09 PT PT147226849T patent/PT2997010T/pt unknown
- 2014-05-09 NO NO14722684A patent/NO2997010T3/no unknown
- 2014-05-09 BR BR112015028599-6A patent/BR112015028599B1/pt active IP Right Grant
- 2014-05-09 UA UAA201512297A patent/UA117485C2/uk unknown
- 2014-05-09 KR KR1020157035329A patent/KR102193270B1/ko active IP Right Grant
- 2014-05-09 RU RU2015153209A patent/RU2667500C2/ru active
- 2014-05-09 MX MX2015015726A patent/MX367797B/es active IP Right Grant
- 2014-05-09 SG SG11201508680VA patent/SG11201508680VA/en unknown
- 2014-05-09 US US14/890,971 patent/US9512299B2/en active Active
- 2014-05-09 CA CA2909890A patent/CA2909890C/en active Active
- 2014-05-09 WO PCT/EP2014/059578 patent/WO2014184116A1/de active Application Filing
- 2014-05-09 DK DK14722684.9T patent/DK2997010T3/en active
- 2014-05-09 HU HUE14722684A patent/HUE036514T2/hu unknown
- 2014-05-09 AU AU2014267409A patent/AU2014267409B2/en active Active
- 2014-05-09 CN CN201480028109.4A patent/CN105228980B/zh active Active
- 2014-05-09 ES ES14722684.9T patent/ES2657926T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105228980A (zh) | 2016-01-06 |
| AU2014267409B2 (en) | 2016-11-10 |
| SG11201508680VA (en) | 2015-11-27 |
| WO2014184116A1 (de) | 2014-11-20 |
| BR112015028599B1 (pt) | 2021-05-18 |
| RU2667500C2 (ru) | 2018-09-21 |
| MX367797B (es) | 2019-09-06 |
| BR112015028599A2 (pt) | 2017-07-25 |
| PT2997010T (pt) | 2018-02-07 |
| RU2015153209A (ru) | 2017-06-19 |
| RU2015153209A3 (de) | 2018-03-14 |
| PL2997010T3 (pl) | 2018-03-30 |
| EP2997010B1 (de) | 2017-11-15 |
| UA117485C2 (uk) | 2018-08-10 |
| CN105228980B (zh) | 2017-12-29 |
| HUE036514T2 (hu) | 2018-07-30 |
| JP6162887B2 (ja) | 2017-07-12 |
| AU2014267409A1 (en) | 2016-01-07 |
| US9512299B2 (en) | 2016-12-06 |
| EP2803660A1 (de) | 2014-11-19 |
| JP2016524635A (ja) | 2016-08-18 |
| EP2997010A1 (de) | 2016-03-23 |
| CA2909890C (en) | 2021-03-16 |
| MX2015015726A (es) | 2016-03-07 |
| ES2657926T3 (es) | 2018-03-07 |
| US20160096951A1 (en) | 2016-04-07 |
| KR20160020434A (ko) | 2016-02-23 |
| NO2997010T3 (de) | 2018-04-14 |
| DK2997010T3 (en) | 2018-02-26 |
| CA2909890A1 (en) | 2014-11-20 |
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